Mesoionic purinone analogs as inhibitors of cyclic-AMP

Michael E. Rogers, Richard A. Glennon, J. Doyle Smith, Marvin R. Boots, Nitin Nanavati, Julie E. Maconaughey, Debbie Aub, Sheree Thomas, R. G. Bass, a...
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J. Med. Chem. 1981, 24, 1284-1287

1284

0.88 (cellulose; BAW). Anal. ( C & I ~ N l l ON~ )C: calcd, 45.27; found, 44.72; H: calcd, 5.70; found, 6.61; S: calcd, 6.72; found, 7.27. S-Adenosyl-l,8-diamino-3-thiooctane (2c). S-Adenosyll&diazid0-3-thiooctane (2d; 280 mg, 0.49 mmol) and triphenylphosphine (420 mg, 1.6 "01) were dissolved in 1mL of dry pyridine, and the resulting solution was kept a t ambient temperature with stirring for 1h, during which time gas evolution (presumably Na) was observed. Ammonium hydroxide (15 M, 300 NL)was then added, and stirring was continued for another 2 h. The excess ammonium hydroxide and pyridine were removed under high vacuum at mom temperature, and the resulting residue waa dissolved in 70 mL of HzO. The aqueous solution was washed with benzene (3 X 50 mL) and ether (3 X 50 mL) and then lyophilized to give 212 mg (82.5%) of free aminonucleoside as a hygroscopicwhite solid NMFt (D20) S 0.67-1.96 (10 H, br, CH2), 2.3-3.06 (7 H, complex, CH,N